Hydrochloric Acid → HCID 54197236, compound

HRID 1283849Notes

Reaction equation

HRID 1283849 reaction equation
II.[CH:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:4].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Cl>[Zn].O1CCCC1>[C:26]([O:25][C:23](=[O:24])[CH2:22][CH:3]([OH:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 807Iodine2×HCID 79177tert-Butyl bromoacetateHCID 21516683HCID 21516683, compound

Product 1

HCID 54197236HCID 54197236, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of 59 g. (0.75 g-atom) of activated zinc in 500 ml. of dry tetrahydrofuran containing a crystal of iodine is brought to reflux under nitrogen. To this is added slowly a solution of 12.1 g. (0.50 mol.) of benzyl 7-formylheptanoate and 117 g. (0.60 mol.) of t-butyl bromoacetate in 500 ml. of dry tetrahydrofuran. Within a few minutes, the solution becomes cloudy and the iodine color disappears, indicating that the reaction has started. After the addition is complete (30 minutes), the mixture is stirred and refluxed for an additional hour. The cooled solution is then poured into 0.1 N hydrochloric acid and the pH adjusted to 2 with 2 N hydrochloric acid. The excess zinc is filtered off and the filtrate thoroughly extracted with ethyl acetate. The combined extracts are dried and concentrated in vacuo to give crude 3-hydroxydecanedioic acid 10-benzyl ester-1-t-butyl ester.

Workup

  1. additionA stirred suspension of 59 g
  2. temperatureto reflux under nitrogen
  3. additionTo this is added slowly a solution of 12.1 g
  4. waitWithin a few minutes
  5. additionAfter the addition
  6. custom(30 minutes)
  7. temperaturerefluxed for an additional hour
  8. filtrationThe excess zinc is filtered off
  9. extractionthe filtrate thoroughly extracted with ethyl acetate
  10. customThe combined extracts are dried
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc8c7d35174b4ac292a7e1c602554aa7
Source dataset
uspto-grants-1976_08
Patent number
US03976660

Reaction notes

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